Posted on August 07, 2018
We had a Gnome Thief named Penny in our game. Her player was devoted to playing Penny in a particular manner—to have her take anything that wasn't nailed down.
Of course, the Cleric didn't take too kindly to that. But with a huge Tiefling Barbarian as her partner, no one protested too much. In fact, she started coming in handy when she passed her ‘check for traps’ and ‘disarm traps’ checks (around 3rd level).
Being the DM, my biggest issue was having to always ask Penny's player if she was sure she wanted to steal something. She could not resist stealing everything in sight, including things in people's pockets. She definitely looted each body following their fights. I had to question her alignment (chaotic good) constantly. The Cleric (lawful good) was always lecturing her on morality.
Then, one day, they agreed to help a local guard captain save a town from undead by locating where the undead were coming from and putting an end to it. Part of that meant finding the scout the man had sent ahead for more information. After managing to wrangle up the party (especially Penny, who wanted to loot the captain's tower) they set off.
They found the scout, but he was partly dead from fending off some zombies earlier.
Penny: Can I pick his pocket?
Me: Of a half-dead soldier? What alignment are you again?
Cleric: You should understand appropriate looting by now.
Penny: Okay, okay.
Finally, after the failed attempts of the Cleric to save the scout, he passed away. The party chopped off his head to make sure he wouldn't rise up as a zombie. Which was smart. But then Penny piped up.
Penny: Now can I pick his pocket?
Tiefling: I don't see why not.
*Party looks at Cleric*
Cleric: Uh, well... I guess that's okay. He's dead.
Me to the Cleric: Didn't you just mention appropriate looting? Off the corpse of a once lawful good scout? What alignment are you again?
Penny: Oh, good point. Shame on you, Cleric.
Party: Yeah, what is your deal, dude?
It become sort of a joke about following the proper etiquette of appropriate looting from there on out. Needless to say, they buried the soldier with all his gear… well, most of it, since Penny then made a secret check to steal whatever money he had on him after the party had packed up to leave.